Abstract
A general strategy for the synthesis of polycyclic polyprenylated acylphloroglucinols is described in which a scalable, Lewis acid catalyzed epoxide-opening cascade cyclization is used to furnish common intermediate 4. The utility of this approach is exemplified by the total syntheses of both ent-nemorosone and (+)-secohyperforin, which were each accomplished in four steps from this intermediate.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Benzophenones / chemical synthesis*
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Benzophenones / chemistry
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Cyclization
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Epoxy Compounds / chemistry*
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Lewis Acids / chemistry*
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Molecular Structure
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Phloroglucinol / analogs & derivatives*
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Phloroglucinol / chemical synthesis
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Phloroglucinol / chemistry
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Stereoisomerism
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Terpenes / chemical synthesis*
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Terpenes / chemistry
Substances
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Benzophenones
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Epoxy Compounds
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Lewis Acids
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Terpenes
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nemorosone
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secohyperforin
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Phloroglucinol